Production of pentachloracetone



. maintaining a temperature 0 UNITED STATES.

PATENT OFFICE.

HYYM. E. BUG, OF ROSELLE, NEW JERSEY, ASSIGNOB TO STANDARD OIL COMPANY, OF BAYONNE, NEW JERSEY, A CORPORATION OF NEW JERSEY.

1,391,757. No Drawing.

The present invention relates to processes for the production of pentachloracetone and will be clearly understoodfrom the following description thereof.

In accordance with the present invention mixtures of chloracetones comprising dichloracetone (asym.) and trichloracetone with smaller, varying proportions of sym. tetrachloracetone and of pentachloracetone, are formed by the reaction of chlorin upon isopropyl alcohol in the presence or absence of water under controlled conditions to minimize the formation of chlorinated hydrocarbons. The proportion of pentachloracetone in such mixtures is always small. The mixture of chloracetones, previously separated from the material fromwhich it is produced, is in turn subjected to the action of .chlorin, preferably while f 70 to 100 C. in the resence of water. Water is. added to t e reacting mixture in such quantities that the HCl produced in the reaction will form therewith a solution having a concentration of approximatel 20% 1101.

In forming the mixture of c loracetones above referred to I prefer to utilize the procedure described in my co-pending application Ser. No. 4217 30, filed of even date herewith. Isopropyl alcohol, which may be ancess,

or may contain water, is subjected chlorin, preferably in exwhile maintaining a temperature etween 35 and 70 0., and preferably 65 C. Under these conditions the formation of chlorinated hydrocarbons is minimized. The reaction may be carried out in any suitable manner, for example, by passing chlorin into a body of isopropyl alcohol or by assing chlorin through a temperature controlled tower in countercurrent to a descending current of the alcohol. The liquid products of reaction are collected and separate by gravity into a heavier, oily layer consisting chiefly of chloracetones and a lighter, aqueous or alcoholic layer contamhydrous to the action of Specification of Letters Yatent.

Patented Sept. 27, 1921.

Application filed November 4, 1920. Serial No. 421,729.

ing chloracetones .in solution. The chloracetones may be salted out from this solution by the addition of suitable inorganic compounds, for example, NaCl or (32131,, and on separation may, if desired, be added to the oily layer above referred to or may be treated separately. The vapor products of reaction may be collected, for example, by absorption in water, in which case the absorber liquid separates into two layers; a heavier, oily layer comprising chiefly mixed chloracetones and an aqueous layer containing HCl. These mixtures of chloracetones may be treated separately or may preferably be combined with those earlier mentioned. The mixed chloracetones have a specific gravity of 1.45 to 1.50 and consist chiefly of di and trichloracetone (such as 1.3.3), with smaller, but varying quantities of tetra and pentachloracetones. When it is attempted to directly chlorinate isopropyl alcohol to pentachloracetone large quantities of highly chlorinated hydrocarbons are formed.

The mixed chloracetones are placed in aand chlorin is passe through, water having added. The amount of water may va but should not be excessively large, in whic case a considerable part of the chloracetones will be dissolved in it. A volume of water equa to that of the chloracetones is found to be satisfactory. During the passage of the chlorin the heat is applied to maintain a temperature of-7O to 100 C. A substantially complete conversion of the lower chloracetones into pentachloracetone is effected in 48. to 60 hours. During the progress of the reaction H01 is formed and it is pre ferred toadd water in such amounts that the HCl concentration of the aqueous solution remains at approximately 20%. The pentachloracetone readily separates from the aqueous liquid by reason of its greater density.

It is readily apparent that the process may be made wholly c -I and subjecting them to t e action of chlorin 70 acetone.

as limitations upon the scope of the inven-. 0. and in the presence of water sufiicient' tion, except in so'far as included in the acto form a solution of the H01 derived from 80 companying claims. a the reaction, of concentration, thereby claim: efiectin conversion of the chloracetones into 1. The process of preparing 'pentapentach oracetone. chloracetone which consists in subjecting 4'. T e process of preparing pentaisopropyl alcohol to the action of chlorin chloracetone which comprises- "'=br 1nging under conditions controlled to produce chlorin into reacting relation with lower chloracetones, :separatin the chloracetones h orgnated acetones at a temperature above to effect their conversion into pentachlor- 5. The process of preparing pentachloracetone which comprises; bringing 40 2. The process of preparing pentachlorin into reacting relatioiif-wf l1 lower chloracetone which consists in subjecting chlorinated acetonesv at a tenifleflfature beisopropyl alcohol to the action of chlorin tween 70 0. and 100, 0. at a temperature between 35 and 70 0., 61' T e process of preparing pentaseparating the chloracetones formed, and chloracetone which comprises bringingsubjectin'g them to the action of chlorin chlorin into reacting relation with lower while maintaining a temperature above chlorinated acetones at a temperature above 70 0., thereby efi'ecting their conversion 70 0., and adding water to efiect solution into R entachloracetone. of hydrochloric acid formed in the reaction.

he process of preparing pentachlor- 7. he process of preparing --pentaacetone which consists in sub'ecting isoprochloracetone which comprises bringing pyl alcohol to the action .0 chlorin at a chlorin into reacting relation' with lower temperature between 35 and 0., sepachlorinated acetones and. adding waterto rating the chldracetones formed, and subform a solution of 20% concentration of the jecting, them to the. action of chlorin while H01 formed in. the-reaction. maintaining a temperature of 70 to 7 I HYYM'E. BU0. 

